Asymmetric nitrogen. 76. Quantum chemical study of geometry and configurational stability of ketenimines
1992
MNDO calculations were carried out of the ground and transitional states of the planar inversion of the N atom for ketenimines containing σ (Me, NH2, OH, OMe, and F) and π (CH = O) acceptor N substituents as well as for C-amino- and C-formylketenimines. Configurationally stable N-amino-, N-alkoxy-, and N-fluoroketenimines (inversion barriers ∼27–45 kcal/mole) are of interest for further experimental stereochemical studies. The geometry of the ketenimine fragment is determined in general bynN-πCC* conjugation. Other orbital and Coulombic interactions affect C- and N-substituent orientation relative to this fragment.
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